Vacation rentals in Shirley

4.93 out of 5 average rating, 237 reviews

A light-filled bedroom features a spacious bed with striped linens, situated next to a cozy sofa. A flat-screen TV is mounted on the wall opposite the bed. A large window allows natural light, with sheer curtains enhancing the bright ambiance.

Apartment in Coram

Private Apartment- close to shops, Pt. Jeff., SBU

Separate apartment with private keyless entrance. Cozy one bedroom king suite and sofa with full pull out bed. Full kitchen and dining area. Bathroom with standing shower. Free parking on premise for up to 2 cars. Quiet, family friendly neighborhood. Located in the heart of Long Island. Close to everything! Wineries, Farms, breweries, golf, shopping, great dining. NYC is a only a train ride away! Conveniently located within a mile of groceries and laundromat. High speed WiFi, 55in smart tv

An expansive deck offers a view of the Great South Bay, with a mix of comfortable seating options, including lounge chairs and a sectional sofa. The area is complemented by manicured green grass and a wooden railing, providing a serene backdrop for outdoor relaxation.

4.98 out of 5 average rating, 226 reviews

Luxurious Waterfront Beach House On The Bay

Relax and enjoy your time at this beautiful east end waterfront getaway. This house is located right on the relaxing and exclusive Great South Bay with private beach... The experience will bring you the feel of tranquility everyone desires with vacationing out east. While offering all the enjoyments the island has at your fingertips. Centrally located to all island destinations. 90 minutes from Manhattan - 15 minutes to West Hampton - 15 minutes to Fire Island Ferrys. Visit top winery’s WiFi

4.86 out of 5 average rating, 130 reviews

Home in Hampton Bays

Hamptons Oceanfront Oasis

Escape the hustle & bustle of city life and unwind at this stunning home in the Hamptons. The oceanfront oasis is the perfect way to wake up to ocean views, beaches and nearby restaurants. Relax on our spacious deck - perfect for morning coffees & sunset cocktails. It is just a short drive to the train station & only 15 minutes from the airport for quick getaways. For your safety, the home is equipped with Ring cameras and one-use key codes. Book now and experience the ultimate Hamptons escape!

Guest suite in Fire Island Pines

The cabin's entrance is framed by lush greenery and flowering plants. A wooden walkway leads to the door, and a small set of steps offers access. The rustic exterior features dark wood siding and a window for natural light.

4.96 out of 5 average rating, 103 reviews

Fire Island Pines: Studio Cabin

Studio cabin (approx. 13.5 x 15 ft.) Functional, basic, rustic, atmospheric—It's just a little cabin in the woods. The shack can accommodate only 2 people max. Queen bed (sheets, blankets) Bathroom (shower/towels) Kitchenette (fridge, microwave, sink, dishwasher, dishes, cutlery, glasses) A/C (window unit) Fan Basic tv Internet Beach chairs/umbrellas, Outside shower The Pines is primarily a gay community, but welcoming to all. We love our wild deer and squirrels but no pets in the cabin

Superhost

A spacious living area features large glass windows that frame a stunning sunset over the water. The open design enhances natural light, illuminating the room's elegant furnishings and wooden accents. A dining table is positioned near the windows, inviting relaxed meals with a view.

Cabin in Shirley

4.83 out of 5 average rating, 193 reviews

A-Frame cabin with private beach & epic sunsets

Just a 1.5 hour drive from NYC, this home is the perfect beach getaway spot, with a few steps from the deck to the private beach with its beautiful view across the Great South Bay. Remote work with stunning water views through the wall of windows & in cold weather light a fire while sunlight floods the living space. Two queen bedrooms & bunk bed room sleeps 6 guests, great for families or a small gathering of friends. 5 min drive to ocean beach with great swimming & surfing at Smith Point.

4.96 out of 5 average rating, 193 reviews

A modern living area features a dark sectional sofa accented by cushions and a stylish area rug. In the background, a dining space with four chairs and a kitchen area is visible. Natural light enters through multiple windows, creating a bright, inviting environment.

Apartment in Medford

Charming 2 Bedroom apartment

Enjoy our charming 2 Bedroom apartment that is in a quiet and friendly neighborhood in a cul-de-sac. Private entrance on first floor of our house with 2 Bedrooms, 1 Bathroom, Living room, Dining area, and a Kitchen. Close to: Main highways (Sunrise HWY/Long Island Expressway), Grocery stores, Winery & Vineyards, Davis park ferry, Downtown Patchogue village (Restaurants, bars, breweries, shopping), Beaches, Top Golf, MacArthur airport, Long Island Community Hospital, St Joseph’s College.

4.96 out of 5 average rating, 167 reviews

Home in Mastic

Family Retreat with Heated Pool, Hot Tub, Sauna.

🛏 6 Bedrooms, 9 beds & 3 Full Baths 🏊‍♂️ Heated Pool & Relaxing Hot Tub 4-person Sauna 🏀 Half Basketball Court & 🏐 Volleyball Area 🏌️‍♂️ Private Golf Putting Green 🔥 Cozy Firepit & Outdoor Lounge Area 🛝 Swing Set & Kid-Friendly Yard 🍽 Fully Stocked Kitchen & Spacious Dining 🌐 High-Speed Wi-Fi & Smart TVs 10 min to Smith Point Beach & Boardwalk 15–20 min to Long Island Wine Country Nearby hiking at Wertheim Wildlife Refuge Short drive to Tanger Outlets & restaurants

Superhost

The open living area features a custom slate pool table with a vibrant arrangement of billiard balls. A modern kitchen is visible in the background, including sleek cabinetry and a refrigerator. A tasteful seating area includes a fireplace and a large wall-mounted television.

4.94 out of 5 average rating, 262 reviews

By NYC & Hamptons - Hot Tub, Pool Table, Speakeasy

Welcome to Coast to Coast - the perfect getaway from NYC! You may have heard about our new little secret - but you’ll have to come see it for yourself to believe it! Step back into prohibition era Long Island in our hidden speakeasy! Right by Smith Point Beach, we provide accommodations that go above and beyond- this is not your average AirBnB! Soak up the sun at one of LI's top beaches, then enjoy complimentary Netflix, Hulu, cable and more while you shoot pool or play games.

4.94 out of 5 average rating, 141 reviews

A cozy living space features exposed wooden beams and natural light streaming through the windows. A small kitchenette with modern appliances is visible, alongside a comfortable sofa and a rustic wooden coffee table. Decorative shelves and a unique tree branch accent add character to the room.

Tiny home in Mastic

Cozy craftsman style home close to beaches

Feel refreshed when you stay in this rustic gem. 10 minutes from the fire island beaches this newly renovated home will take your breath away. 20 minutes from local wineries theres no shortage of things to do. This is a single dwelling home. There is a basement apartment with a separate entrance. The tenant does not have access to the house. Everything pictured is yours to use! Kick your feet up and enjoy the details of this handcrafted home. Tree house inside and out!

4.95 out of 5 average rating, 141 reviews

A cozy living area features a plush gray couch adorned with decorative pillows. Vibrant blue walls complement the stylish kitchen cabinetry in the background. A large flat-screen television displays a scenic beach image, while a sleek desk sits nearby. Soft lighting adds to the inviting ambiance.

Apartment in Shirley

Boho Beach Vibez Retreat! Private entrance

"Experience a different kind of stay with our unique Airbnb, the 'Boho Beach Vibez” This cozy 1-bedroom apartment , that’s approximately 500sqft is situated on the first level of our home with a separate entrance . Located in a prime area of our town, you'll find yourself just minutes away from all the stores, restaurants, highways, and within walking distance of hiking trails, the Carman’s river, and 5 miles from Smith Point beach. NOTE : hosts live on top level .

Superhost

A spacious living room features a large sectional sofa adorned with colorful cushions, offering comfort and relaxation. A sleek television is mounted on the wall, while natural light streams through wide windows, illuminating a wooden coffee table and a decorative fireplace in the corner.

Home in Mastic

4.86 out of 5 average rating, 133 reviews

Cozy home. Comfy living

The whole group will enjoy access to everything from this centrally located home. three comfy bedroom, two bathrooms, large living room, dining and kitchen. close to the beach, nature reserved, kayaking, sky diving and Tanger outlet mall, restaurant and all the fast food located nearby. long island vast array of winery and farms stand etc. Guest is expected to follow house rules. 15 mins after check out time is given after that fees will incur at nightly rate

A well-maintained putting green is positioned in the front yard, surrounded by soft turf and bordered by gravel. Small flags are placed on the green, with nearby shrubs and trees adding to the outdoor landscape. The house is visible in the background.

4.94 out of 5 average rating, 176 reviews

Beach Waterview, 3 KING Beds, Golf Putting Green

Take it easy at this 3 story waterview beach home with a putting green and fire pit. The Bellport Bay is across the street. Shirley Beach: 0.4 mile walk Smith Point Beach: 1.8 miles Featuring: 3 luxurious KING beds 👑 (and 2 fulls) Watch Netflix, Disney+ on the 70" living room TV and 3 50" bedroom TVs Fully equiped kitchen/dining room Enjoy BBQ Grill, fire pit on premium soft turf Highspeed mesh WiFi, keyless entry.

Popular amenities for Shirley vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Shirley

An open-concept living area is showcased with a light gray sofa adorned with patterned pillows. A plush area rug lies beneath it, while wooden cabinets and essential appliances are visible in the kitchenette area, complemented by a patterned floor mat.

4.86 out of 5 average rating, 64 reviews

Home Sweet Home by the Beach

4.91 out of 5 average rating, 47 reviews

A two-story blue house is set in a well-maintained yard with green grass and neatly trimmed hedges. A double garage doors are visible on the left, and a front porch with steps leads to the main entrance, framed by decorative shrubs.

Home in Center Moriches

Peaceful and Bright 4 Bedroom Getaway Home

4.88 out of 5 average rating, 25 reviews

Apartment in Medford

Medford Seclusive Getaway

4.98 out of 5 average rating, 48 reviews

Home in Centereach

Cozy Modern Getaway

5 out of 5 average rating, 18 reviews

A charming two-story house features a light-colored exterior with dark accents. A welcoming front porch leads to the entrance, and a grassy yard surrounds the property, creating a peaceful atmosphere. Nearby trees and accessible parking are visible, enhancing the inviting setting.

Home in Mastic Beach

Newly Renovated Home in Mastic Beach!

4.97 out of 5 average rating, 31 reviews

The exterior of a two-story home is showcased, featuring a light-colored facade and a welcoming front porch. An inviting turquoise door is centered, flanked by large windows. Lush greenery and landscaped gardens surround the entrance, enhancing the peaceful ambiance of the property.

Home in East Patchogue

Bayside Breeze

4.92 out of 5 average rating, 48 reviews

Home in Mastic

Cozy Guest Suite 10 min to Ocean